Iodine-Mediated Oxidative Coupling of Hydroxamic Acids with Amines towards a New Peptide-Bond Formation

Abstract

An efficient and straightforward approach for the coupling of N^α-protected hydroxamic acids with an amino component in the presence of iodine is delineated. The reaction is mediated by the formation of unstable but reactive acyl nitroso intermediates. The peptide hydroxamic acids were found to be useful substrates in coupling reactions.

Key words

N^α-protected amino hydroxamic acids - amino acid esters - oxidative acylation - acyl nitroso intermediate - iodine

• References and Notes

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• 29 General Procedure for the Preparation of Dipeptide Esters 7a–l* To a solution of N^α-protected amino hydroxamic acid 5 (1.0 equiv) in DMSO (5 mL), I₂ (0.3 equiv), and amino acid ester 6 (1.2 equiv) were added at r.t. and stirred. After completion of the reaction, as monitored by TLC analysis (5–30 min), the solvent was removed under reduced pressure, and the crude residue was diluted with EtOAc (20 mL). The organic layer was washed with 10% Na₂CO₃ (15 mL), 10% citric acid (15 mL), H₂O (10 mL) and brine solution (10 mL), dried over anhydrous Na₂SO₄, and evaporated in vacuo. The crude residue was purified through silica gel column chromatography (100–200 mesh), EtOAc–hexane (40:60) as eluent to obtain dipeptide esters.
• 30 Methyl 2-[2-({[(4aH-Fluoren-9-yl)methoxy]carbonyl}-amino)propanamido]-3-phenylpropanoate [Fmoc-Ala-Phe-OMe, 7a]. ¹H NMR (300 MHz, CDCl₃): δ = 1.33 (d, J = 3 Hz, 3H , CH₃), 3.12–3.17 (m, 2 H, CH₂Ph), 3.70 (s, 3 H, OCH₃), 4.05–4.09 (m, 1 H, δCH, NHCHCH₃, Ala), 4.17–4.20 (m, 1 H, αCH,-NHCHCH₂, Phe), 4.31 (t, J = 9 Hz, 1 H, CH₂CH, Fmoc), 4.34 (d, J = 9 Hz, 2 H, CH ₂CH, Fmoc), 5.32 (br d, J = 6 Hz, 1 H, NH, Fmoc), 6.46 (br d, J = 6 Hz, 1 H, NH, amide), 7.06–7.76 (m, 13 H, 5 CH, Ph, 8 CH, Fmoc). ¹³C NMR (75 MHz, CDCl₃): δ = 18.6 (CβAla), 37.9 (CβPhe), 47.2 (CαFmoc), 50.2 (CαAla), 52.5 (Me), 53.3 (CαPhe), 67.2 (CβFmoc), 120.1, 125.1, 127.3, 127.8, 128.6, 128.7, 129.3 (CH, Ar), 135.7 (C, Ar), 141.4 and 143.9 (C, Fmoc), 156.4 (C=O, Fmoc), 171.7 and 171.8 (C=O). HRMS: m/z [M + H]⁺ calcd for C₂₈H₂₉N₂O₅: 473.2076; found: 473.2062.
• 31 Methyl 2-[2-({[(4aH-Fluoren-9-yl)methoxy]carbonyl}-amino)methylbutanamido]propanoate [Fmoc-Val-Ala-OMe (7b)] ¹H NMR (300 MHz, CDCl₃): δ = 0.95 [d, J = 5 Hz, 6 H, CHCH(CH ₃)₂], 1.26 (d, J = 5 Hz, 3 H, CHCH ₃), 2.04–2.10 [m, 1 H, CHCH(CH₃)₂], 3.69 (s, 3 H, OCH₃), 4.18–4.25 (m, 2 H, δCH, NHCHCH, Val, αCH, NHCHCH₃, Ala), 4.35 (t, J = 3 Hz, 1 H, CH₂CH, Fmoc), 4.42 (d, J = 5 Hz, 2 H, CH ₂CH, Fmoc), 5.28 (br d, J = 6 Hz, 1 H, NH, Fmoc), 6.42 (br d, J = 5 Hz, 1 H, NH, amide), 7.26–7.77 (m, 8 H, 8 CH, Fmoc). ¹³C NMR (75 MHz, CDCl₃): δ = 17.5 (CβAla), 19.1 (CγVal), 31.1 (CβVal), 47.3 (CαFmoc), 50.1 (CαAla), 52.3 (Me), 59.0 (CαVal), 67.2 (CβFmoc), 120.1, 125.1, 127.2, 127.8 (CH, Fmoc), 141.4 and 143.8 (C, Fmoc), 156.4 (C=O, Fmoc), 172.2 and 172.3 (C=O). HRMS: m/z [M + H]⁺ calcd for C₂₄H₂₉N₂O₅: 425.2076; found: 425.2082.
• 32 Optical purity of products 7b,c was determined by HPLC. See Supporting Information for the HPLC chromatograms.